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Weinreb Amides in Carbene Chemistry: A Time-Resolved IR Investigation into a Potential Intramolecular Stabilization Mechanism

Evans, AS; Sundaram, GSM; Sassmannshausen, J; Toscano, JP; Tippmann, EM; (2010) Weinreb Amides in Carbene Chemistry: A Time-Resolved IR Investigation into a Potential Intramolecular Stabilization Mechanism. ORG LETT , 12 (20) 4616 - 4619. 10.1021/ol101946u.

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Abstract

A chloromethylhydroxamiccarbene was generated photochemically in an attempt to form an intramolecularly stabilized carbene. A rapidly formed intermediate at 1645 cm(-1) decayed with an observed rate of 1.99 x 10(6) s(-1). Other intermediates were also observed. These also decayed, albeit much more slowly (k(obs) = 3.47 x 10(3) and 1.98 x 10(4) s(-1)). Multiple intermediates are apparently a function of both the proximal N,O-dimethylhydroxamic ester and multiple conformers of both the carbene and precursor

Type:Article
Title:Weinreb Amides in Carbene Chemistry: A Time-Resolved IR Investigation into a Potential Intramolecular Stabilization Mechanism
DOI:10.1021/ol101946u
Keywords:SOLVATION, REARRANGEMENT, ULTRAFAST, N,N-DIETHYLDIAZOACETAMIDE, DICHLOROCARBENE, PHOTOCHEMISTRY, SPECTROSCOPY, COMPLEXES, DYNAMICS, BENZENE
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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